[23] Southend 2-1 Leyton Orient [10] 2021-04-24 14:00
Stadium: Roots Hall Round: 44
Referee: Trevor Kettle Home Manager: Phil Brown Away Manager: Joel Joshua Frederick McAnuff
Head to Head
| Anglia - League 2 | 2020/12/29 19:00 | Leyton Orient v Southend | L | 2-0 |
| Anglia - EFL Trophy | 2019/09/03 18:45 | Leyton Orient v Southend | L | 2-0 |
| Europa - Amicale | 2018/07/28 14:00 | Leyton Orient v Southend | D | 2-2 |
| Anglia - EFL Trophy | 2016/10/04 18:45 | Southend v Leyton Orient | W | 1-0 |
| Meciuri amicale internationale intercluburi | 2015/08/02 12:00 | Southend v Leyton Orient | L | 0-1 |
Home History
| Anglia - League 2 | 2021/04/20 18:00 | Colchester v Southend | L | 2-0 |
| Anglia - League 2 | 2021/04/17 11:30 | Exeter v Southend | D | 0-0 |
| Anglia - League 2 | 2021/04/10 14:00 | Southend v Crawley Town | D | 0-0 |
| Anglia - League 2 | 2021/04/06 17:30 | Morecambe v Southend | D | 1-1 |
| Anglia - League 2 | 2021/04/03 12:00 | Southend v Carlisle | L | 0-2 |
| Anglia - League 2 | 2021/03/27 15:00 | Harrogate Town v Southend | W | 0-1 |
| Anglia - League 2 | 2021/03/23 19:00 | Southend v Walsall | D | 0-0 |
| Anglia - League 2 | 2021/03/20 15:00 | Scunthorpe v Southend | D | 1-1 |
Away History
| Anglia - League 2 | 2021/04/20 18:00 | Leyton Orient v Cambridge Utd | L | 2-4 |
| Anglia - League 2 | 2021/04/17 11:30 | Leyton Orient v Barrow | W | 2-0 |
| Anglia - League 2 | 2021/04/13 18:00 | Harrogate Town v Leyton Orient | D | 2-2 |
| Anglia - League 2 | 2021/04/10 14:00 | Cheltenham v Leyton Orient | L | 1-0 |
| Anglia - League 2 | 2021/04/05 14:00 | Leyton Orient v Walsall | D | 0-0 |
| Anglia - League 2 | 2021/04/02 14:00 | Mansfield v Leyton Orient | W | 0-2 |
| Anglia - League 2 | 2021/03/27 15:00 | Leyton Orient v Oldham | W | 2-1 |
| Anglia - League 2 | 2021/03/23 18:30 | Carlisle v Leyton Orient | W | 0-1 |
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